I may have to test the font thing, I've never tried to transfer fonts. I've got two hackintosh's and both work great, though it took a little tweaking to get them there, but once they were setup, they just work. I haven't had the same luck with laptops though, which is why I ended up just buying a macbook.

There are certain things that just work better on mac, and I use mine mostly for audio production. I use external soundcards and for whatever reason, Windows cannot run the gear at the same low latencies as OSX without losing audio quality, stutters, crackling, etc. I find MIDI devices also tend to be a lot easier to get started with on Mac, you plug them in and they mostly just work. Windows already needs a driver and it's annoying

Illustrator and photoshop on mac I tend to like, I can't speak for newer CS6 versions, but in the cs5 i have, your palettes and tools and all that are their own windows, its handy when your working across multiple monitors because you can stretch things out, you're not confined to 1 window like are on...Windows. I prefer it anyhow

I know for my own needs, there are just some things that I prefer Mac for. some things just work better, some things don't though, goes both ways which is why I like to keep at least one of each around. I used to have a linux machine as well, but now days anything I might have needed linux for, or wanted it for, I can do just as easily on Mac